I approached the street with the first drunken guy cautiously and made my way back down it to the safety of my front door. As I rounded the corner, I noticed there was an older cleaning lady in one of the offices standing outside having a cigarette break. She must have heard me approaching as […]
Crossdressing
A Crossdresser Steps Out9
Despite listening out hard for people approaching (footsteps) I failed to notice the guy I was about to cross right in front of. I didn’t see him until the last minute and by this time has was no more than 10 feet from me approaching from the side. My heart skipped a few beats. I […]
A Crossdresser Steps Out8
I had to quickly readjust my skirt to look respectable but from their range, it wouldn’t have been possible to see much anyway. I was surprised neither of them turned around with the clicking of my heels, they both seemed to be really getting into their conversation – whatever that was about. Knowing that they […]
A Crossdresser Steps Out7
Rather than go home now, I continued up another street totally unplanned, this street was much quieter and not so well lit up although it was terraced houses on either side with no dark recesses for the potential of any lurkers. Because of the high walls, I was much more conscious of the loud […]
A Crossdresser Steps Out6
I turned right off this road and continued my journey up the street, heart racing in case of any further encounters.. I carried on with my venture, I got to the crossroads at the end of the street, my initial plan was to take a right but this would miss out a good 20 minutes […]
A Crossdresser Steps Out5
As we passed I could feel him quite unashamedly staring over at me, looking at me up and down but I didn’t acknowledge him. I knew – from the lack of footsteps- that the drunk chap had stopped and was watching me as I walked away from him; then it happened…… He started shouting towards […]
A Crossdresser Steps Out4
Unfortunately, as this was more of an access road rather than a street it was not really possible to cross over to the other side to avoid getting too close to him – plus it didn’t help matters much since he was staggering down the middle of the road. Being the only ‘”female” at that […]
A Crossdresser Steps Out3
This was my first time out in my 4″ heels and after being out on several occasions in my 5″ ones I thought it would be quite easy to walk but as usual, being accustomed to walking on soft carpet disillusions you into believing that walking outside is no different. I quickly realized how wrong […]
A Crossdresser Steps Out2
Next on was my clip-on earrings and a splash of Chanel perfume. I checked myself in front of my full-length mirror, adjusted my skirt so that my stocking tops were properly covered, and grabbed my handbag before heading for the front door. I stood and listened for a while to make sure none of my […]
A Crossdresser Steps Out1
It must be several months ago now and I had an unfortunate encounter with a drunk. It was getting late but as it was mid-week I figured that it ought to be quite quiet. I was dressed in my ‘office attire’ of white blouse, black jacket, and mini skirt. I decided to wear my 4″ […]